Hydrolysis of used ionic liquid catalyst for disposal

ABSTRACT

We provide a process and apparatus for preparing a used catalyst for disposal, comprising:
         a. hydrolyzing a used ionic liquid catalyst comprising an anhydrous metal halide to produce a hydrolyzed product; and   b. separating the hydrolyzed product into a liquid phase and a solid phase; wherein the liquid phase comprises a non-water-reactive aqueous phase and a hydrocarbon phase; and wherein the solid phase comprises a solid portion of the hydrolyzed product, that is not water reactive. A vessel is used for the hydrolyzing and a separator is used for the separating.

TECHNICAL FIELD

This application is directed to a process and apparatus for preparing aused ionic liquid catalyst for disposal.

BACKGROUND

Ionic liquid catalysts need to be safely disposed of after use. Withouttreatment, they can be highly water reactive and unsafe to handle ordispose of.

SUMMARY

This application provides a process and apparatus for preparing a usedcatalyst for disposal, comprising:

a. hydrolyzing a used ionic liquid catalyst comprising an anhydrousmetal halide to produce a hydrolyzed product; and

b. separating the hydrolyzed product into a liquid phase and a solidphase; wherein the liquid phase comprises a non-water-reactive aqueousphase and a hydrocarbon phase; and wherein the solid phase comprises asolid portion of the hydrolyzed product, that is not water reactive. Theapparatus comprises a vessel used to hydrolyze the used ionic liquidcatalyst and a separator.

BRIEF DESCRIPTION OF THE DRAWINGS

FIG. 1 is a diagram of a flow chart with one embodiment for hydrolysisof ionic liquid catalyst.

DETAILED. DESCRIPTION

Anhydrous metal-halide-containing used ionic liquid catalyst is treatedfor safe and economic disposal by hydrolyzing the used ionic liquidcatalyst followed by separation which produces a non-water-reactiveaqueous phase, a hydrocarbon phase and a solid phase.

Prior to the treatment by the process the used catalyst is waterreactive and unsuitable for disposal by usual methods. “Water reactive”means that the composition will violently react with moisture, sometimesleading to release of toxic gases, explosions, or fire. Water reactivesubstances are dangerous when wet because they undergo a chemicalreaction with water. This reaction can release a gas that presents atoxic health hazard. In addition, the heat generated when water contactssuch materials is often enough for the mixture to spontaneously combustor explode.

Ionic Liquid Catalyst

Ionic liquid catalysts comprising an anhydrous metal halide are veryeffective for catalyzing a hydrocarbon conversion process. Examples ofhydrocarbon conversion processes are paraffin alkylation, olefindimerization, olefin oligomerization, concurrent alkylation andoligomerization, isomerization, and aromatic alkylation. The hydrocarbonconversion process can be one used to make gasoline, middle distillate,base oil, or petrochemical components.

The ionic liquid catalyst comprising an anhydrous metal halide iscomposed of at least two components which form a complex. The firstcomponent of the ionic liquid catalyst comprises an anhydrous metalhalide Which provides Lewis Acid functionality to the catalyst. Themetal halide is selected from compounds of Group 13 metals, includinganhydrous aluminum halides, alkyl aluminum halide, gallium halide, andalkyl gallium halide. Specific metal halides, such as AlCl₃, AlBr₃,GaCl₃, GaBr₃, InCl₃, InBr₃, and mixtures thereof could be in the usedionic liquid catalyst. The periodic table by the International Union ofPure and Applied Chemistry (IUPAC), version date 22 Jun. 2007, is usedfor defining the Group 13 metals.

In order to maintain the catalytic activity of the anhydrous metalhalide containing ionic liquid catalyst, the metal halide is kept in ananhydrous condition. Anhydrous metal halides are water reactive whichmeans the anhydrous metal halides react with moisture in the atmosphere,in hydrocarbon feeds, or in water. The reaction with moisture tends tobe very vigorous and generates toxic hydrogen halide gas and thereaction converts a portion or all of the metal halides into metalhydroxide and hydrated metal halides.

The second component making up the ionic liquid catalyst is an organicsalt or mixture of salts. These salts can be characterized by thegeneral formula Q+A−, wherein Q+ is an ammonium, phosphonium, boronium,iodonium, or sulfonium cation and A− is a negatively charged ion such asCl⁻, Br⁻, ClO₄ ⁻, NO₃ ⁻, BF₄ ⁻, BCl₄ ⁻, PF₆ ⁻, SbF₆ ⁻, AlCl₄ ⁻, TaF₆ ⁻,CuCl₂ ⁻, FeCl₃ ⁻, HSO₃ ⁻, RSO₃ ⁻, SO₃CF₃ ⁻, alkyl-aryl sulfonatc, andbenzene sulfonate (e.g., 3-sulfurtrioxyphenyl). In one embodiment thesecond component is selected from those having quaternary ammoniumhalides containing one or more alkyl moieties having from about 1 toabout 12 carbon atoms, such as, for example, trimethylaminehydrochloride, methyltributylammonium halide, or substitutedheterocyclic ammonium halide compounds, such ashydrocarbyl-substituted-pyridinium halide compounds for example1-butylpyridinium halide, benzylpyridinium halide, orhydrocarbyl-substituted-imidazolium halides, such as for example,1-ethyl-3-methyl-imidazolium chloride.

In one embodiment, the second component making up the ionic liquidcatalyst is an organic salt that is hygroscopic in nature and has atendency to attract and hold water molecules from the surroundingenvironment. With these ionic liquid catalysts, in order to maintain theintegrity of the ionic liquid catalyst and its catalytic performance,both the anhydrous metal halides and the organic salts are thoroughlydried before the catalyst synthesis, and moisture-free conditions aremaintained during the catalytic reaction.

In one embodiment the ionic liquid catalyst is selected from the groupconsisting of hydrocarbyl-substituted-pyridinium chloroaluminate,hydrocarbyl-substituted-imidazolium chloroaluminate, quaternary aminechloroaluminate, trialkyl amine hydrogen chloride chloroaluminate, alkylpyridine hydrogen chloride chloroaluminate, and mixtures thereof. Forexample, the used ionic liquid catalyst can be an acidic halaaluminateionic liquid, such as an alkyl substituted pyridinium chloroaluminate oran alkyl substituted imidazolium chloroaluminate of the general formulasA and B, respectively.

In the formulas A and B; R, R₁, R₂, and R₃ are H, methyl, ethyl, propyl,butyl, pentyl or hexyl group, X is a chloroaluminate. In one embodimentthe X is AlCl₄ ⁻, Al₂Cl₇ ⁻, or Al₃Cl₁₀ ⁻. In the formulas A and B, R,R₁, R₂ and R₃ may or may not be the same. In one embodiment the ionicliquid catalyst is N-butylpyridiniumheptachlorodialtiminate[NBuPy⁺][Al₃Cl₇ ⁻]. In one embodiment the usedionic liquid catalyst is 1-Ethyl-3-methylimidazoliumheptachlorodialuminate [emim⁺][Al₂Cl₇ ⁻].

Used Ionic Liquid Catalyst

After the ionic liquid catalyst has been used to catalyze a hydrocarbonconversion process it can become deactivated, or no longer needed, forfurther hydrocarbon conversions. We refer to this catalyst as used ionicliquid catalyst.

In one embodiment the used ionic liquid catalyst comprises a cationselected from the group of an alkyl-pyridinium, an alkyl-imidazolium, ora mixture thereof. In another embodiment the used ionic liquid catalystcan have the general formula RR′R″N H⁺ Al₂Cl₇ ⁻, wherein N is a nitrogencontaining group, and wherein RR′ and R″ are alkyl groups containing 1to 12 carbons, and where RR′ and R″ may or may not be the same.

In one embodiment, the used ionic liquid catalyst is the full chargefrom a hydrocarbon conversion process. In another embodiment, the usedionic liquid catalyst is a portion of the full charge of catalyst from ahydrocarbon conversion process. In one embodiment, less than a fullcharge of used ionic liquid catalyst is removed from a hydrocarbonconversion reactor or process unit such that the hydrocarbon conversionreactor or process unit operates continuously. The used ionic liquidcatalyst can be drained from the process unit, and may also be referredto as spent ionic liquid catalyst. For example, the used ionic liquidcatalyst can be less than 20 wt %, less than 15 wt %, less than 10 wt %,less than 5 wt %, or less than 1 wt % of the full charge of catalyst inthe hydrocarbon conversion process unit. By removing less than the fullcharge of catalyst, the hydrocarbon conversion process can operatecontinuously, with gradual removal and addition of fresh or reactivatedionic liquid catalyst without stopping or disrupting the process.

Residual Hydrocarbon or Conjunct Polymer

In one embodiment the used ionic liquid catalyst additionally comprisesresidual hydrocarbon or conjunct polymer. Residual hydrocarbon orconjunct polymer can be formed and built up in the used ionic liquidcatalyst during hydrocarbon conversion processes. The term conjunctpolymer was first used by Pines and Ipatieff to distinguish thesepolymeric molecules from other polymers. Unlike some other polymerswhich are compounds formed from repeating units of smaller molecules bycontrolled or semi-controlled polymerizations, “conjunct polymers” are“pseudo-polymeric” compounds formed asymmetrically from two or morereacting units by concurrent acid-catalyzed transformations includingpolymerization, alkylation, cyclization, additions, eliminations andhydride transfer reactions. Consequently, the produced“pseudo-polymeric” may include a large number of compounds with varyingstructures and substitution patterns. The skeletal structures of“conjunct polymers”, therefore, range from the very simple linearmolecules to very complex multi-ring featured molecules. Some examplesof the likely polymeric species in conjunct polymers were reported byMiron et. al. (Journal of Chemical and Engineering Data, 1963), andPines (Chem. Tech., 1982). Conjunct polymers are also commonly known tothose in the refining industry as “red oils” due to their reddish-ambercolor or “acid-soluble oils” due to their high uptake in the catalystphase where paraffinic products and hydrocarbons with low olefinicityand low functional groups are usually immiscible in the catalyst phase.In this application, the term “conjunct polymers” also includes ASOs(acid-soluble-oils), red oils, and C12+ alkylates. Residual hydrocarboncan be unreacted starting materials from the hydrocarbon conversionprocess, or products from the hydrocarbon conversion process that arenot separately collected.

One way to dispose of used ionic liquid catalyst is incineration.Incineration is not only an expensive disposal option but also thewater-reactive nature of the used ionic liquid catalyst makesincineration difficult. As the used ionic liquid catalyst is exposed tothe moisture during the incineration step, it can generate toxic andcorrosive gas and corrosive materials that can damage the incinerationequipment. Thus, there is a need for a safer and more cost efficientdisposal process for used ionic liquid catalysts. We have found thatspent ionic liquid catalyst can be converted to environmentally friendlymaterials by controlled hydrolysis and can be disposed of in a costefficient manner.

Hydrolysis

The used ionic liquid is hydrolyzed with water or with a basic solution.The hydrolysis conditions can be chosen carefully so that the reactionheat is controlled and the hazardous gas formed during the hydrolysis iscaptured by the hydrolysis solution medium. In one embodiment, thehydrolysis uses a basic solution comprising water and a base that isstrong enough to neutralize an acid formed by the used ionic liquidcatalyst and water. In one embodiment the base that can be used for thehydrolysis is a base that hydrolyzes completely, and forms a basicsolution with a pH of 10 or higher. Examples of bases include LiOH,NaOH, KOH, CsOH, RbOH, Mg(OH)₂, Ca(OH)₂, Sr(OH)₂, NH₄OH, Ba(OH)₂, andmixtures thereof. In one embodiment, the cation of the base is an alkalimetal, an alkaline earth metal, or ammonium hydroxide. In anotherembodiment, the hydrolysis vessel holds a basic solution comprising abase selected from the group consisting of LiOH, NaOH, KOH, CsOH, RbOH,Mg(OH)2, Ca(OH)2, Sr(OH)2, NH4OH, Ba(OH)2, and mixtures thereof.

The basic solution can contain from 1 wt % to 60 wt % of the base, 5 wt% to 30 wt % of the base, 8 wt % to 25 wt % of the base, or 10 wt % to20 wt % of the base, depending on the solubility and strength of thebase used.

In one embodiment, the used ionic liquid catalyst and basic solution aremixed together at a molar ratio of used ionic liquid catalyst to base of0.5:1 to 1:20, 1:1 to 1:15, or 1:1 to 1:10. The temperature under whichthe hydrolysis is performed is from −20° C. to 90° C. The pressure underwhich the hydrolysis is performed is from 80 to 2500 kPa. In oneembodiment, the hydrolyzing is done at ambient temperature and pressure.In one embodiment, the hydrolyzing occurs in less than a week, less than50 hours, and in some embodiments can occur in less than 10 hours, orless than 1 hour. In one embodiment the hydrolyzing occurs between 1minutes and 60 minutes, between 10 minutes and 45 minutes, or between 15minutes and 40 minutes. In one embodiment the hydrolysis proceedscontinuously by adding used ionic liquid catalyst into the hydrolysisvessel while the hydrolyzed product is taken out. Residence time of themixture of used ionic liquid catalyst and aqueous solution in thehydrolysis vessel of the continuous unit can range from 10 minutes to 10hours.

In one embodiment the hydrolysis reaction can be controlled carefully inorder to control the reaction temperature and pressure. To control theexotherm associated with the hydrolysis, one could adjust the feed rateof ionic liquid to the hydrolysis solution medium. A cooling coil can beadded to control the hydrolysis temperature and to minimize thevaporization of hydrolysis medium, which is typicallywater. In someembodiments it is desirable to control the hydrolysis temperature toless than 90° C., less than 70° C., or less than 50° C.

The hydrolysis can be performed with or withoutstirring or withrecirculation through a pump. In one embodiment the used ionic liquidcatalyst is added slowly to the basic solution. Adding the used ionicliquid catalyst slowly can help control the hydrolysis temperature. Thehydrolysis can be performed continuously, semi-continuously, or inbatches.

In one embodiment, the vessel used for the hydrolyzing is fabricated ofa metal, a plastic, a resin, or a glass. The vessel can be agitated ormixed by any suitable method such as stirring or recirculation aroundthe vessel via a pump. In one embodiment the vessel is designed to giveturbulent flow so that thorough mixing will result. Since the hydrolysiscan be quite exothermic, in some embodiments, cooling coil(s) or fan(s)can be used to maintain the proper temperature.

After the hydrolysis, the final pH of the mixture of the used ionicliquid catalyst and the basic solution can be adjusted. Alternatively,the pH of the basic solution can be adjusted to reach a target pH fordisposal. In one embodiment, the hydrolysis conditions are controlled toreach an acceptable, near neutral pH for the non-water-reactive aqueousphase. At a near neutral pH, the aqueous phase can be treated as anon-hazardous waste stream and can be sent to non-hazardous effluentwaste handling facilities. In one embodiment, the pH of thenon-water-reactive aqueous phase is 4 to 10, 5 to 9, or 6 to 8.

In one embodiment, a hydrogen halide gas is evolved during thehydrolysis and the hydrogen halide gas dissolves into the basic solutionand is neutralized (i.e., reacted with the base). For example, whenhydrolyzing a used ionic liquid catalyst comprising a chloroaluminate,hydrogen chloride can be evolved and dissolved into the basic solution.Capturing the hydrogen chloride into the basic solution and neutralizingit prevents the release of a toxic and corrosive gas into theatmosphere.

The hydrolysis step produces solid particles that form a slurry in theliquid phase. For example, when hydrolyzing a used ionic liquid catalystcomprising a chloroaluminate, a slurry containing solid precipitatescomprising aluminum hydroxide, aluminum oxide and hydrated aluminumchloride forms.

Separation of Liquid and Solid Phases

The hydrolyzed product containing solid and liquid phases is separatedby a separator, employing, for example, filtration or centrifugation toseparate the liquid phase from the solid phase. In one embodiment, theliquid phase contains mostly residual hydrocarbon and the aqueous phaseof the hydrolyzed product, which is non-water-reactive. In oneembodiment, the separated liquid phase contains less than 5 wt %, lessthan 2 wt %, or less than 1 wt % of the solid material in the hydrolyzedproduct.

Either prior to or during the liquid-solid separation, an organicpolymer or inorganic coagulant can be added to the hydrolyzed product tomake the separation of the liquid phase from the solid phase moreefficient and/or to reduce any chemically bound water in the solidphase.

Filtration can be a method used for separation of the hydrolyzed productinto the liquid phase and the solid phase. Any filter and filter mediathat effects good separation of the liquid phase from the solid phasecan be used. The filter is a semi-permeable barrier placed perpendicularto or across a liquid flow. The filter media and depth is sizedaccording to the size and amount of particles in the solid phase. In oneembodiment, the filter is either a gravity or pressure rapid filter.

The filter can operate either up-flow, down-flow, or at anglesin-between. Examples of filter media that can be used in the filterinclude a deep bed (e.g., greater than 3″ up to 50″) of sand oranthracite on a large particle bed support. Mixed media filter beds canalso be used.

In one embodiment, the solid phase is rinsed with a hydrocarbon, water,or both to remove hydrocarbon products and/or water soluble productsheld in the solid phase. The rinsate can be added to the liquid phase orseparately handled.

Solid Phase

The solid phase separated from the hydrolyzed product comprises a solidphase of the hydrolyzed product that is not water reactive. It can besafely handled or disposed of as waste or could be sent to acoker unit.In some embodiments, the solid phase requires no further processing tobe disposed of in a landfill. In some embodiments the solid wastecomprises residual materials that require it be disposed of as hazardouswaste.

In one embodiment, the solid phase comprises reaction products formed bythe hydrolysis of the anhydrous metal halide in the used ionic liquid.For example, when hydrolyzing a used ionic liquid catalyst comprising achloroaluminate, a slurry containing solid precipitates comprisingaluminum hydroxide, aluminum oxide and hydrated aluminum chloride forms.In one embodiment, greater than 75 wt %, greater than 80 wt %, orgreater than 90 wt % of the anhydrous metal halide is hydrolyzed andcollected in the solid phase. In one embodiment, the solid phasecomprises less than 40 wt %, less than 30 wt %, or less than 20 wt % ofwater and residual hydrocarbon.

In one embodiment, the solid phase comprises metal that can come fromone or more corrosion metals, or products thereof. Examples of corrosionmetals are those included in steel alloys, such as Al, Co, Cr, Cu, Fe,Mn, Mo, Nb, Ni, Ti, V, W, and mixtures thereof. Examples of products ofcorrosion metals are metal hydroxides, oxides, or chlorides. Removal ofthe corrosion metals can make the liquid phase more suitable for wasteeffluent treatment or other uses.

Separating Hydrocarbon Phase from the Liquid Phase

In one embodiment, the liquid phase is further separated into an aqueousphase and a hydrocarbon phase in a liquid/liquid separator. Theseparating is done using any liquid/liquid separator that separates thecomponents of the liquid phase between two immiscible solvent phases ofdifferent densities. The separating can be done using gravity, such asin a separatory funnel.or dropping funnel. The separating can also bedone using a centrifuge, especially where the volume to be separated isvery large or the separation is desired to be done quickly, such as inless than an hour, less than 30 minutes, or less than 10 minutes.

The aqueous phase can be easily handled by several means, including bydisposal as aqueous waste, sent to an effluent treatment facility, orsent to a facility to recover NaOH. The hydrocarbon phase can be used insubsequent refining operations as fuel or recycled in a refineryhydrocarbon pool. For example, the hydrocarbon phase can be separatedand used as a solvent or feed to a refining process. In one embodiment,the hydrocarbon phase can be used as a feed for a coker unit, a feed toa base oil or distillate plant; or used as a fuel oil.

EXAMPLES Example 1 Used Ionic Liquid Catalyst Comprising Anhydrous MetalHalide

In this example we used N-butylpyridinium heptachlorodialuminatc(C₅H₅NC₄H₉Al₂Cl₇) ionic liquid catalyst. This catalyst had the followingcomposition:

Element Wt % Al 12.4 Cl 56.5 C 24.6 H 3.2 N 3.3

The above catalyst was used for C3/C4 olefins alkylation with isobutaneto make alkylate gasoline. During the alkylation the used catalystaccumulated 5 wt % of conjunct polymer. The used catalyst alsoaccumulated trace amounts of Fe, Ni, Cu and Cr from corrosion byproductsin the alkylation process.

Example 2 Hydrolysis of Used Ionic Liquid Catalyst

173.3 g of 15 wt % NaOH solution was prepared in a 1 L beaker equippedwith an overhead stirrer. While stirring, 58.66 g of the used ionicliquid catalyst from Example 1 was added slowly to the NaOH solutionover a 36 minute period at a rate to control the exotherm from thehydrolysis to less than 50 deg C. A brown slurry was formed and thefinal pH of the solution with the brown slurry was about 5. The brownslurry was filtered to capture an aluminum hydroxide/oxide solid as awet filter cake.

The filter cake was rinsed with heptane and de-ionized water to removeany strippable hydrocarbon from the filter cake and to add thestrippable hydrocarbon to the liquid filtrate. 78.8 g of rinsed wetfilter cake was recovered. The liquid filtrate was separated further toa hydrocarbon phase and an aqueous phase using a separatory funnel. Thehydrocarbon phase was dried to remove the heptane solvent, and 0.34 g ofheavy hydrocarbon having a brownish yellow color was recovered.

The boiling point distribution of the recovered hydrocarbon phase wasmeasured by gas chromatography for high temperature distillation usingASTM D 6352-04 (Reapproved 2009), “Standard Test Method for BoilingRange Distribution of Petroleum Distillates in Boiling Range from 174 to700° C. by Gas Chromatography”, and the results are shown below.

% Temperature, C. (F.) IBP 204 (399) 10 303 (578) 30 354 (670) 50 394(742) 70 443 (830) 90  539 (1003) FBP  720 (1328)

The boiling point distribution data showed that the recoveredhydrocarbon phase had a final boiling point greater than 700 deg. C.This heavy hydrocarbon would be a useful product for many purposes,including a feed for a coker unit or a fuel oil.

Example 3 Material Balance of Hydrolyzed Product Streams

Elemental analyses of the aqueous phase and solid phase from Example 2were performed. The elemental analysis showed that the aqueous phasecontained mainly Na, Al, N, C, and very low corrosion metal ionconcentrations (below instrument detection limits). The elementalanalysis of the solid phase (rinsed wet filter cake) from Example 2indicated that the bulk (i.e., greater than 70 wt %) of the corrosionmetals were captured in the solid phase.

Elemental material balances around Example 2 were calculated tounderstand how the key elements of the feed composition of the usedionic liquid catalyst and basic solution were redistributed in thehydrolyzed product phases. The tables below show the distribution of keyelements in the feeds (ionic liquid catalyst+NaOH solution) and in theresulting different hydrolyzed product phases (hydrocarbon phase,non-water-reactive aqueous phase, and the solid phase).

Feed Composition: Used Ionic Liquid Conjunct NaOH Element Cat., Wt %Polymer, Wt % Solution, Wt % C 86 14 0 N 100 0 0 Cl 99 1 0 Al 100 0 0 Na0 0 100 Fe 100 0 0

Product Composition: Aqueous Hydrocarbon Solid Phase (Wet Element Phase,Wt % Phase, Wt % Filter Cake), Wt % C 68 2.1 30 N 52 <1 48 Cl 82 <1 18Al 0.3 <1 99.7 Na 84 <1 16 Fe 3 0 97

The compositional analysis indicated that greater than 99.5 wt % of theanhydrous aluminum chloride in the used ionic liquid catalyst wasconverted to solids (e.g., aluminum hydroxide and aluminum oxide) andcollected in the wet filter cake. It is believed that most of theN-butylpyridinium chloride stayed intact during the hydrolysis process.The compositional analysis suggested that over 50 wt % of theN-butylpyridinium chloride was dissolved in the aqueous phase and therest was deposited on the wet filter cake. Most of the NaOH solution wasconverted to NaCl and was dissolved in the aqueous phase. Most of thecorrosion metal products, as noted by Fe, were deposited in the solidphase that was collected in the wet filter cake.

The transitional term “comprising”, which is synonymous with“including,” “containing,” or “characterized by,” is inclusive oropen-ended and does not exclude additional, unrecited elements or methodsteps. The transitional phrase “consisting of excludes any element,step, or ingredient not specified in the claim. The transitional phrase“consisting essentially of limits the scope of a claim to the specifiedmaterials or steps “and those that do not materially affect the basicand novel characteristic(s)” of the claimed invention.

For the purposes of this specification and appended claims, unlessotherwise indicated, all numbers expressing quantities, percentages orproportions, and other numerical values used in the specification andclaims, are to be understood as being modified in all instances by theterm “about.” Furthermore, all ranges disclosed herein are inclusive ofthe endpoints and are independently combinable. Whenever a numericalrange with a lower limit and an upper limit are disclosed, any numberfalling within the range is also specifically disclosed.

Any term, abbreviation or shorthand not defined is understood to havethe ordinary meaning used by a person skilled in the art at the time theapplication is filed. The singular forms “a,” “an,” and “the,” includeplural references unless expressly and unequivocally limited to oneinstance.

All of the publications, patents and patent applications cited in thisapplication are herein incorporated by reference in their entirety tothe same extent as if the disclosure of each individual publication,patent application or patent was specifically and individually indicatedto be incorporated by reference in its entirety.

This written description uses examples to disclose the invention,including the best mode, and also to enable any person skilled in theart to make and use the invention. Many modifications of the exemplaryembodiments of the invention disclosed above will readily occur to thoseskilled in the art. Accordingly, the invention is to be construed asincluding all structure and methods that fall within the scope of theappended claims. Unless otherwise specified, the recitation of a genusof elements, materials or other components, from which an individualcomponent or mixture of components can be selected, is intended toinclude all possible sub-generic combinations of the listed componentsand mixtures thereof.

What is claimed is:
 1. A process for preparing a used catalyst for safedisposal, comprising: a. hydrolyzing a used ionic liquid catalystcomprising an anhydrous metal halide to produce a hydrolyzed product,wherein a hydrogen halide gas is evolved during the hydrolyzing and thehydrogen halide qas is dissolved into a basic solution used for thehydrolyzing and the hydrogen halide qas is neutralized; b. separatingthe hydrolyzed product into a liquid phase and a solid phase; whereinthe liquid phase comprises a non-water-reactive aqueous phase having apH of 4 to 10 and a hydrocarbon phase; and wherein the solid phase isnot water reactive.
 2. The process of claim 1, wherein the used ionicliquid catalyst is selected from the group consisting of ahydrocarbyl-substituted-pyridinium chloroaluminate, ahydrocarbyl-substituted-imidazolium chloroaluminate, a quaternary aminechloroaluminate, a trialkyl amine hydrogen chloride chloroaluminate, analkyl pyridine hydrogen chloride chloroaluminate, and mixtures thereof.3. The process of claim 1, wherein the anhydrous metal halide isselected from the group consisting of AlCl₃, AlBr₃, GaCl₃, GaBr₃, InCl₃,InBr₃, and mixtures thereof.
 4. The process of claim 1, wherein thehydrolyzing is done with a basic solution comprising a base selectedfrom the group consisting of LiOH, NaOH, KOH, CsOH, RbOH, Mg(OH)₂,Ca(OH)₂, Sr(OH)₂, NH₄OH, Ba(OH)₂, and mixtures thereof.
 5. The processof claim 1, wherein less than a full charge of the used ionic liquidcatalyst is removed from a hydrocarbon conversion process unit such thatthe hydrocarbon conversion process unit operates continuously.
 6. Theprocess of claim 1, wherein the used ionic liquid catalyst comprisesconjunct polymer.
 7. The process of claim 1, additionally comprisingseparating the non-water-reactive aqueous phase from the hydrocarbonphase.
 8. (canceled)
 9. The process of claim 1, wherein the hydrolyzingproceeds continuously by adding the used ionic liquid catalyst to ahydrolysis vessel while the hydrolyzed product is taken out of thehydrolysis vessel.
 10. The process of claim 1, wherein the used ionicliquid catalyst comprises one or more corrosion metals other thanaluminum and the one or more corrosion metals, or products thereof, arecollected in the solid phase.
 11. The process of claim 1, whereingreater than 80 wt % of the anhydrous metal halide is hydrolyzed andcollected in the solid phase.
 12. An apparatus for preparing a usedcatalyst for disposal, comprising: a. a vessel used to hydrolyze a usedionic liquid catalyst comprising an anhydrous metal halide, to produce ahydrolyzed product; and b. a separator used to separate a liquid phaseand a solid phase from the hydrolyzed product; wherein the liquid phasecomprises a non-water-reactive aqueous phase and a hydrocarbon phase;and wherein the solid phase comprises a solid portion of the hydrolyzedproduct, that is not water reactive.
 13. The apparatus of claim 12,wherein the used ionic liquid catalyst is selected from the groupconsisting of a hydrocarbyl-substituted-pyridinium chloroaluminate, ahydrocarbyl-substituted-imidazolium chloroaluminate, a quaternary aminechloroaluminate, a trialkyl amine hydrogen chloride chloroaluminate, analkyl pyridine hydrogen chloride chloroaluminate, and mixtures thereof.14. The apparatus of claim 12, wherein the anhydrous metal halide isselected from the group consisting of AlCl₃, AlBr₃, GaCl₃, GaBr₃, InCl₃,InBr₃, and mixtures thereof.
 15. The apparatus of claim 12, wherein thevessel used to hydrolyze holds a basic solution comprising a baseselected from the group consisting of LiOH, NaOH, KOH, CsOH, RbOH,Mg(OH)₂, Ca(OH)₂, Sr(OH)₂, NH₄OH, Ba(OH)₂, and mixtures thereof.
 16. Theapparatus of claim 12, wherein less than a full charge of the used ionicliquid catalyst is removed from a hydrocarbon conversion process unitsuch that the hydrocarbon conversion process unit operates continuously.17. The apparatus of claim 12, wherein the used ionic liquid catalystcomprises conjunct polymer.
 18. The apparatus of claim 12, additionallycomprising a liquid/liquid separator used to separate the liquid phaseinto the non-water-reactive aqueous phase from the hydrocarbon phase.19. The apparatus of claim 12, wherein a hydrogen halide gas is evolvedin the vessel and the hydrogen halide gas is dissolved into a basicsolution held in the vessel, and is neutralized.
 20. The apparatus ofclaim 12, wherein the used ionic liquid catalyst comprises one or morecorrosion metals and the one or more corrosion metals, or productsthereof, are collected in the solid phase.
 21. The apparatus of claim12, wherein a hydrolysis is performed continuously by adding the usedionic liquid catalyst to the vessel while the hydrolyzed product istaken out of the vessel.
 22. The apparatus of claim 12, wherein greaterthan 80 wt % of the anhydrous metal halide is hydrolyzed and collectedin the solid phase.
 23. The process of claim 1, wherein the used ionicliquid catalyst and the basic solution are mixed together at a molarratio of used ionic liquid catalyst to a base of 0.5:1 to 1:20.
 24. Theprocess of claim 1, wherein a pH of the basic solution is adjusted toreach a target pH for disposal.
 25. The process of claim 24, wherein thetarget pH for disposal enables the non-water-reactive aqueous phase tobe sent to a non-hazardous effluent waste handling facility.
 26. Theprocess of claim 1, wherein the pH is 5 to
 9. 27. The process of claim1, wherein the solid phase contains solid precipitates comprisinghydrated aluminum chloride.
 28. The process of claim 1, wherein thehydrolyzing is performed with control of a hydrolysis temperature. 29.(canceled)